What Contractor Software Actually Costs in September 2026 (Six Vendors, Priced at Real Headcounts)

Ask three contractors what their software costs and you will get three headline prices and no idea what anyone actually pays. That is not the contractors' fault. Most vendors advertise the cheapest seat of the cheapest plan and then price the plan you need by seat band, by feature tier, and by add-on. This guide prices six tools the way you would be billed: at a real headcount, with the add-ons a working shop turns on. Every number was read from the vendor's own pricing page in September 2026 and is linked so you can check it.

Why is the advertised price rarely the price a contractor pays?

Because the entry price is usually one seat of a plan that lacks the features you bought the software for. Three mechanisms drive the gap: seat bands (the same plan costs more at 5 users than at 1), feature gating (automated reminders or recurring billing live one tier up), and add-ons (marketing, AI phone answering, pipeline tools sold separately). A fourth, processing fees, scales with revenue rather than headcount and quietly outgrows the subscription on a busy shop.

The honest way to compare is therefore arithmetic, not a feature checklist: the tier that has the features you will use, at the headcount you will have in a year, plus required add-ons, plus what it costs to take a card. We laid out that method in flat-rate vs per-feature pricing; this post does the arithmetic for you.

What does each vendor charge for a solo operator?

At one user the field is close and cheap. Jobber Core is $49/month month-to-month or $29/month prepaid annually. Housecall Pro Basic is $79/month, or $59 billed annually. HoneyBook Starter is $29/month. Dubsado Starter is $20/month and includes three users. Tabsy Express is $39/month with every feature included. ServiceTitan publishes no prices at any size.

The catch at this size is feature gating rather than price. Jobber Core, Housecall Pro Basic and HoneyBook Starter are the plans with the fewest automations, so the solo operator who wants online approvals, automatic reminders and recurring invoices is often looking at the next tier within a few weeks. Compare what each entry plan actually includes before you compare the sticker.

What does a 5-person crew pay per month and per year?

This is where the advertised prices fall apart, because four of the six vendors price a 5-person crew differently from a solo operator. Month-to-month, September 2026:

• Jobber Grow, 5-user band: $299/month, or $229/month prepaid annually. That is $3,588/year month-to-month, $2,748 annually. Jobber Connect at 5 users (fewer features) is $199/month, $2,388/year.
• Housecall Pro Essentials (5 users included): $189/month, or $149 billed annually. $2,268/year month-to-month, $1,788 annually.
• HoneyBook Premium (the only HoneyBook plan that allows more than 2 team members): $129/month, or $109 billed yearly. $1,548/year month-to-month, $1,308 yearly.
• Dubsado Premier: $40/month with 3 users included; users 4 and 5 fall into the next user bracket. $480/year before that bracket.
• Tabsy LPM Growth (5 users, every feature): $150/month, or $120 billed annually. $1,800/year month-to-month, $1,440 annually.
• ServiceTitan: no published price; quoted per technician, typically with a paid implementation. Ask for a written 12-month quote.

Two things stand out. Jobber's Grow plan is $199/month in the price round-ups because that is its one-user band; at five users it is $299. And the cheapest tools at this size, HoneyBook and Dubsado, are cheaper because they are desk-based client platforms with no dispatching and lighter project management, not because they undercut the field-service tools on the same job. Cheaper is only better if it does the work.

What happens at 10 users?

Seat bands and per-user fees compound. Jobber Grow at the 10-user band is $399/month month-to-month ($299 prepaid annually), so $4,788/year. Housecall Pro MAX includes 8 users at $329/month; users 9 and 10 are $75/month each on MAX, so a 10-person shop is about $479/month, $5,748/year month-to-month. HoneyBook Premium stays at $129/month because it does not cap team members. Dubsado Premier adds user brackets above three. Tabsy LPM Team (10 users) is $250/month, $3,000/year, or $2,400 billed annually. ServiceTitan remains quote-only.

If you expect to hire, this is the row to compare, not the solo row. A per-seat model charges you more exactly when new hires are already straining cash.

How much do add-ons and per-user fees change the total?

Enough to reorder the list. Jobber sells its Marketing Suite for $99/month, its AI Receptionist for $29/month and Pipeline for $49/month, and charges $29/month for each user beyond a seat band. A 5-person Jobber Grow shop that turns on the Marketing Suite is at $398/month, $4,776/year. Housecall Pro charges $100/month per extra user on Essentials and $75/month on MAX, so one hire beyond the included seats costs more than most vendors' entire entry plan. HoneyBook gates automations and scheduling below Essentials, so the "add-on" is a tier upgrade. Tabsy has no paid feature add-ons; the only optional extras are storage, at $3.99/month for 100 GB or $5.99/month for 200 GB.

Processing fees are the add-on nobody lists. Tabsy passes through Stripe's published US rate of 2.9% + $0.30 per card charge (stripe.com/pricing) with ACH lower and no margin added; Housecall Pro advertises card rates "as low as" 2.59% and 1% for bank payments; HoneyBook lists 2.7% + 10 cents on higher tiers and 1.5% for bank transfers. On $40,000 a month of collections, a tenth of a percent is $40 a month, so read the fee schedule, not the software price, if you take a lot of cards.

How should a contractor use these numbers?

Write down three figures: your headcount in twelve months, the two or three features that would actually shorten your collection time, and your monthly card volume. Then price every tool at that headcount and tier, add the add-ons you would turn on, and add the processing fee on your volume. The result is one number per vendor, and it is frequently the reverse of the headline ranking. For the full head-to-head on each vendor, with the same September 2026 sources, see Tabsy vs Jobber, Tabsy vs Housecall Pro, Tabsy vs HoneyBook, Tabsy vs Dubsado and Tabsy vs ServiceTitan, or the ranked buyer's guide.

Disclosure: this guide is published by Tabsy, which has an obvious interest in the comparison. Competitor prices are the vendors' public list prices in USD, month-to-month unless stated, read in September 2026 and re-verified quarterly; they exclude sales tax and introductory discounts. See our editorial standards.